


Learning to fly

by itzteegan



Category: Supernatural
Genre: AU, Alternate Universe, Alternate Universe - Racing, Anal Fingering, Anal Sex, Bottom Castiel (Supernatural), Bottom Castiel/Top Dean Winchester, Castiel (Supernatural) Topping From the Bottom, Destiel - Freeform, Fear of Flying, Flying, Gay Sex, M/M, Pilots, Power Bottom Castiel (Supernatural), Racing, Shameless Smut, Smut, Top Dean Winchester, Topping from the Bottom, safe sex
Language: English
Status: Completed
Published: 2019-07-12
Updated: 2019-07-12
Packaged: 2020-06-27 03:06:53
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,650
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19781974
Author URL: https://archiveofourown.org/users/itzteegan/pseuds/itzteegan
Summary: Dean has grown up in the racing business, so to him, speed is no big deal. What is, however, is flying, and he has no intention of coming close to climbing into a plane. A dare taken on a whim, however, has him facing down his fear, and damn if the pilot doesn't have him actually wanting to fly.





	Learning to fly

**Author's Note:**

  * For [ZarauthForsaken](https://archiveofourown.org/users/ZarauthForsaken/gifts).



"I don't trust wings that don't move, it's just not proper wings!"

"Well I don't trust spinning razor blades. They could cut off a bird's head or clip a wing!"

Dean sighed as he took a sip of the pretentiously expensive wine that the event offered. Which one he was at, he couldn't even remember, his mother went to so many of them. He usually could weasle his way out of them, but not every time, and this was one of those times that no excuse was good enough. So he plastered a grin on his face and put on one of his good suits, and when he arrived he made a beeline straight for the open bar. Of course, all they really had to drink was different kinds of wine and a few cocktails, and while he would have preferred a beer, he grabbed a simple red and figured alcohol was alcohol.

Scanning the room, he took in the other people gathered. Besides his own family - his mom and dad and brother, Sam, who had taken break from studying for the bar to attend - there seemed to just be an amalgamation of attendees. A few lower-tier actors and actresses, a couple of other racers, like himself, and plenty of people he didn't recognise outright. His father was currently ensconced in a conversation with an older gentleman with long, greying hair, an immaculately trimmed beard, and a suit that made him look like he'd stepped out of the pages of GQ. He had briefly caught his name when he'd introduced himself to his dad. What was it ... Cain? Was that his first or last name? Dean couldn't even remember, couldn't really bring himself to care as he tilted the glass and finished off the rest of the wine before he requested another from the bartender.

"What about you?" was suddenly asked, and after a few moments of silence, he realised that he was the one being asked.

"What now?" he asked to clarify, new glass of wine in hand.

Cain was the one who had asked, apparently, as he repeated his question. "What's your stance? Airplane or helicopter?"

"Neither," he answered honestly. "I don't trust anything that takes my feet off the ground. If people were meant to fly, we'd have wings."

"Ah, because driving is so much safer, Mr. Winchester?" Cain asked, referring to his status as top driver for his sponsor.

Dean clicked his tongue and winked. "I'm a lot more in control on the ground than in the air. If I crash, I'm not just gonna free fall."

"It's not quite as simple as that," someone else interjected, and Dean opened his mouth to shoot of a snarky remark when the bluest of blue eyes seemed to paralyse the words before they left his mouth. This other man slowly approached the small grouping that Cain, Dean, and Dean's father made, drawing abreast to Cain, and it was then he noticed there was a vague familial resemblance, though it could have been Dean's imagination.

Clearing his throat, Dean tried to clear the stuck words as he countered with the only thing he could think of. "Oh yeah?" _Nice, great job, Dean. Fucking brilliant._

If he noticed Dean's lack of brilliant response, he didn't call it out. Instead, he replied, "Yes. In fact, depending on several different factors and the reasons for the crash, it can end quite well. On the other hand, far more people die behind the wheel than via airplane crash."

Dean rolled his eyes. "That's because a lot more people drive than fly. And besides, not everybody that gets behind the wheel is a great driver. Like me." _Good recovery?_ _Nah, not really._ _Fuck._ _What is wrong with me?_

The man raised an eyebrow as he raised his glass to take a drink before he responded. "Oh you are, are you? One of those speed demons even outside of the track, I take it?"

"Hey, if I wasn't any good on the track, I wouldn't be any good off it."

He rolled his eyes and shook his head, and Cain of all people interjected. "Oh c'mon, Cas, just because you don't like racing doesn't mean it doesn't take some skill!"

Cas. So that was his name. An odd one, for sure, but Dean had heard worse. And it seemed that this Cas wasn't exactly keen on racing. Which, he knew it wasn't everybody's cup of tea, but questioning Dean's driving skills on top of that? And advocating the death traps known as airplanes? Oh, he was asking for it. Dean's mother wouldn't want him to make a scene, and so he wouldn't, but he did step closer to Cas, drawing himself up to his full height and pleased that it appeared he had about an inch on the guy, on a good day. "What, you don't think I'm any good?"

He shrugged. "I just don't think something that is taught to teenagers in school is necessarily a skill. Unlike piloting."

Oh, them's was fightin' words. "You don't think so? Care for a demonstration? Or maybe a few lessons?"

Cas smirked and heaven help him if Dean didn't gulp a little bit at the action. "Only if you'll agree to fly with me."

Fuck, Dean hated catches. Ordinarily he would have refused outright the second that the prospect of leaving the ground had come into play. But there were eyes on him, not just his father's and Cain's, but it seemed their discussion had drawn some attention. Attention that included his mother's gaze, in that tone that plainly meant, _Play nice._

So, fuck it. Like it or not, he would play nice. He might die in the process, but if he did then he supposed it was the ultimate "I told you so" move. Despite the way anxiety squeezed his gut at the thought of even getting in an airplane, he struck a nonchalant pose and replied with, "You got a deal."

With the wicked grin that crossed Cas' face, Dean was never more sure that he might actually die.

+

No, scratch that. He was definitely going to die.

Dean was initially going to give Cas a go round in his car, but Bobby was busy some needed repairs, and while Dean was eager to show him what all was involved with racing and take him for a spin, he wasn't so arrogant as to take the car out when it needed work done. And so they'd ended up at a small municipal airport where Cas had escorted him to a small prop plane that Dean was certain was made out of tinfoil and prayers. The apprehension must have shown on his face, as Cas asked him if he wanted to back out of it, but Dean had never been a quitter. So he'd plastered on a smile, acted like everything was fine, and silently prayed to whatever god might hear him to please allow him to return to the ground in one piece.

The takeoff wasn't so bad, and for just a split-second, Dean was actually enjoying himself. But then the nose tipped upward and they actually started climbing and Dean was tempted to start saying some Hail Marys just because what the fuck else were you supposed to do? He clutched the arm rests with an iron grip as Cas ascended, and when he got the plane to its suitable cruising altitude, he levelled it off and shot Dean a grin. This one was nothing like the one he'd given him at the event, full of evil malice and obvious plotting. No, this one was relaxed and content and damnit if this was on the ground, Dean knew he could have appreciated it far better. "Go ahead, check out the view," Cas urged, and Dean gulped for a moment before he screwed up his courage.

_When in Rome ..._

He only got the briefest glance of the ground before he slammed himself back in the seat, gripping the seat with a bruising force.

Cas seemed to notice as he asked, "What's wrong?"

"I, uh, well you see, the thing is ..." Dean hemmed and hawed, but really, there was no other way to say it. "I'm afraid of heights, okay?"

The other man laughed outright. "Are you kidding me?" The glare from Dean confirmed that he was not, in fact, joking about it, which lead Cas to draw the conclusion of, "So that's why you don't like flying at all."

"Hey, lots of people are afraid of heights. It's not a big deal," Dean protested, not at all sputtering.

"I didn't say it was," Cas countered smoothly without missing a beat.

The rest of the flight went just fine, at least the way Cas would tell it. The turbulence they ran into had Dean regretting every single thing he'd ever done in his life, and as Cas began the descent to land, Dean had started chanting the Lord's Prayer in his head because it was the only thing he could think of to do. How he'd not had a heart attack or a stroke due to stress, he had no idea, but Cas delivered him to the ground safe and in one piece, just as he'd promised. And he didn't even mention the way that Dean's legs wobbled as he got out of the plane, only asking when Dean would return the favour.

Now that he was back on solid ground and feeling better, Dean was feeling much more like himself as he flashed the man a grin. "Repairs should be done by tomorrow, if you want me to take you for a spin."

Cas nodded. "I would like that."

_It's a date,_ Dean thought, and almost immediately shook his head. _No, it's not a date. Why would my mind immediately go there?_ For that, he had no immediate answers.

+

The next day, Dean was back in his element, and he was feeling it. Ah, the smell of motor oil and gasoline and hot asphalt just did something to him, spoke to something deep in his psyche. Turning to Cas, he saw that the guy was in about the same position as he had been the previous day, and while he'd been planning on some doughnuts or something to try to freak him out as a joke, he well remembered how he'd felt with the tables turned and how Cas kept things as smooth sailing as he could. Because of that, as they piled into the car and buckled up their restraints, Dean had no intentions of practical jokes anymore.

Instead, he kept it smooth as he drove the track, increasing his speed until he was comfortable with it. Out of the corner of his eye, he noticed Cas grabbing onto the seat. He couldn't resist the little jab this time as he remarked, "What, scared just because you're on the ground?"

"I am not scared," Cas insisted. "Just uncomfortable."

"Sure, Cas," Dean replied in that flippant Marcia Brady tone, dropping it as he continued the drive. Even if he hadn’t wanted to take the car out for a spin to test about the repairs and upgrades took, he never passed up an opportunity for a drive. There was just something about driving, about leaning into the car and pushing it to its limits, feeling the speed and the tug of the g’s as he made his way around the track … god, but it was exhilarating. Cas remained white-knuckled for most of the drive, but toward the end Dean noticed it seemed like he was letting up just a little bit. Instead of sitting there tense, body tight, he seemed to let up and relax just a little bit, shoulders dropping and opening up his chest more. Dean valiantly fought to focus on the track ahead of him when really he wanted to look at the man beside him, for reasons he didn’t quite understand.

As they stepped out after Dean brought the car to a stop, he asked Cas, “So? Whadya think?”

Cas gave him a small smile, one that made his heart felt like it stopped for a moment as he replied, “That wasn’t too bad.”

_Yeah, I guess it wasn’t, was it?_

+

Oh how naive he had been.

How foolish to think it would be nothing more than introducing someone to racing while simultaneously facing his own fears of flying. Because as time passed and as he spent more time in Cas’ plane and Cas spent more time in Baby, the closer they became and the more they realised that … they liked it that way. Not that they liked the respective circumstances – though they each started to at least come to terms with how flying and racing was not as bad as they’d initially thought – but that they liked to be _together_ , no matter what was going on. At first, it had been subtle. Making more and more plans together, spending more and more time with each other either at the airport or the track. And then that extended to off hours as well, where they’d grab a coffee after their sessions, or even a meal if it was late enough.

Which, increasingly, it was.

So really, it should have been no surprise that they ended up at Dean’s one night, Cas pushed up against the wall, shirt half off, pants unbuttoned. It was just a natural progression of the build-up that had started at the soiree, something that had started without either of them truly knowing it. Dean made a mental note to thank his mother for dragging him there, but that note was quickly buried as his fingertips brushed against Cas’ hips, encircling his waist, and there was the softest, sweetest moan that emanated from the back of the other man’s throat as Dean pulled him close.

Dean’s lips traced over Cas’ jawline, making a nonsensical pathway down the side of his throat. Their bodies had naturally slotted together so that Cas’ thigh was pressing ever so slightly against Dean’s growing erection and vice versa. When Dean’s tongue shot out and licked a narrow strip up Cas’ throat before he lightly sank his teeth into the skin, Cas involuntarily bucked against him. That only served to spur Dean on even further, teasing and nipping at the sensitive skin until Cas was clutching at him, a moaning mess, pleading, “Dean, let’s … let’s get to the bed.”

And Dean certainly wasn’t averse to that.

Stumbling in the semi-darkness of Dean’s apartment, they wiggled out of the rest of their clothes and Dean searched his dresser for what he needed. With just a little bit of work – and a slight bit of panic on his part when he couldn’t immediately find them – he grabbed the lube and the condom and returned to the bed, laying Cas out with a passionate kiss that left both of them dizzy. Warming the lube in his fingers, he gave Cas’ dick a few strokes before his fingers made their way further south and teased Cas’ opening, circling it and just barely penetrating it. Cas grit his teeth, head flopped back on the pillow as Dean teased him, not only there but by dragging his teeth across his chest, ghosting over his nipples before biting at his ribs. His voice was hoarse with need as he groaned, “Dean, _please_ …”

“I know, I know,” Dean murmured, taking that as the hint to stop fucking around and start the fucking. Not knowing Cas’ experience level – they hadn’t really talked about it before they dove in, a theme that was quickly becoming typical for their relationship, so Dean was unsure if Cas needed thorough prep or not – Dean decided to err on the side of caution as he slipped a well-lubed finger inside Cas. The moan he let loose was practically unholy and Dean stopped all other ministrations just so he could watch him. Watch the way his bright blue eyes closed as he was overwhelmed with sensation, the way his full lips slightly parted, the way his dark hair spread over the pillow, the way his throat was so openly bared as his back arched ever so slightly to the intrusion. Dean felt the ring of muscle relax fairly quickly, so he added a second finger, just to make sure Cas was good with this, and by the way he accommodated the stretch well, it seemed he was no stranger to this dance. Which Dean counted as a plus because _goddamn_ he suddenly had never wanted to be inside somebody so badly.

Despite his growing suspicion that Cas was no blushing virgin, he was still surprised when Cas suddenly grabbed him by his shoulders and flipped them both over, grabbing the condom and smoothing it over Dean’s dick, causing his hips to twitch as he moaned. “I’ll take it from here, cowboy,” he said, his voice low as he straddled Dean, lining himself up. “After all …” that little imp _winked_ , “… I’m not afraid of heights.

Any smart retort Dean might have had on deck completely fled his mind as Cas sank down on his length at the same time. He couldn’t even find it in himself to be annoyed as he breathed deeply in and out of his nose, restraining himself from moving until Cas got himself settled. Dean wasn’t exactly _small_ , but Cas seemed practically made for him as their hips met and he took just a few moments to get used to the stretch before he placed his hands on Dean’s chest and started to slowly rock into a rhythm. Dean flexed his own hips, testing how Cas took the movement, and if the way that he moaned and dug his fingernails into Dean’s chest was any indication, he liked it. And so Dean kept it up, just slowly meeting his thrusts, letting Cas dictate the pace as the other man swerved his hips and ground into Dean’s pelvis, taking him as deep as he possibly could. Dean’s hands wandered until he gripped Cas by the hips, and Cas gave him a devious little half-smile as he threw his head back in reckless abandon as he increased his pace.

The inside of Dean’s apartment was littered with moans and gasps and, if anyone had even so much as come to the door, they would have well known exactly what was going on. There was nothing that could make either of them care, however, if anyone could hear them or not because it felt so damn _good._ Dean was no stranger to quick trysts or even relationships, though he was usually too busy with work to invest much in something like that. But Cas … Cas was different, somehow, and something just made him want to _try_. _Wait, why am I thinking about this during sex?_ While he was able to conjure up enough concentration to wonder about it, his mind immediately left him once more as Cas twisted his hips _just right_ and Dean inhaled sharply as he bit at his lip, pouring what concentration he could come up with into not giving into the orgasm that was teasing at him.

Cas leaned over to seal his lips over Dean’s, and Dean took the opportunity to tangle his fingers in Cas’ dark hair as he pounded into the man above him. Cas may have set the pace but Dean followed exquisitely, not the kind of person to just sit idly by as his lover got them both off. No, he was a full participant, and gladly, swallowing each and every moan that came out of Cas as if it was a gift from god. Which, it might as well have been. Dean felt like he could have survived off of that alone, if given the choice, the way it made his chest feel warm and how it made him feel … _Complete? Is that what I feel?_ It was a new sensation, one he couldn’t recall feeling before, but he didn’t have the time to contemplate it with the way that Cas was moving and groaning and the way he had to bite back his own moans because if his concentration slipped for just a moment, it would all be over.

The way Cas looked at him as he hovered over him, the way his eyes narrowed slightly, he was smouldering, there was really no other way to describe it. Dean would have normally reserved such a sentiment for cheesy romance novels and bodice-rippers, but fuck if they weren’t actually right, at least in this case. With his rumpled hair and his blown pupils and the breathless look about him, Cas looked absolutely beautiful, and Dean knew somewhere, in the back of his mind, that this was the only sight he ever wanted to see in his bed. Maybe it seemed like a bit of a hasty thought to have, especially during their first time, but the sentiment was there regardless and Dean just went with the flow as Cas’ face tightened and his hips trembled and he murmured, “Dean, I’m close.”

He reached down to grasp Cas’ cock in his hand, giving it a few tugs as he replied, his voice low and husky, “Then come on, Cas, I’m ready.”

Cas didn’t need much more motivation than that as he shook, thick ropes landing on Dean’s abs and chest as he fucked Dean even through his orgasm. With his free hand, Dean gripped his hip, keeping up the pace even as Cas started to falter, finding his own end soon after. As they both settled into the afterglow, Cas collapsed against Dean’s chest, ignoring the mess for the moment as they both just basked in the moment. Dean reached up to ruffle his hair and, while he didn’t want to admit, _he knew_ …

He knew what it was like to truly fly. And he never wanted to come back down.

**Author's Note:**

> There will be a sequel to this as well, though I'm not sure when I'll get to writing it. Hopefully sooner rather than later!


End file.
